DE2640542A1 - AZO DYES - Google Patents

Description

The invention relates to azo dyes of the formula I free from sulfonic acid groups

I.
in the

A is the remainder of a diazo component,

B the remainder of a coupling component and

R is hydrogen, halogen, an optionally substituted hydrocarbon radical, optionally substituted alkoxy or aroxy or substituted amino.

As diazo components to amines of the aromatic-carbocyclic series, in particular of the naphthalene and especially of the benzene series, are optionally substituted by halogen, nitro, carboxyl, alkoxycarbonyl, trifluoromethyl, alkyl, aryl _s alkoxy, SCN, alkylsulfonyl, arylsulfonyl, carbamoyl, sulfamoyl or arylazo may be substituted.

Furthermore, heterocyclic diazo components are also particularly suitable those of the thiazole, benzthiazole, benzisothiazole, thiadiazole,. Triazole, pyrazole, indazole or thiophene series, which can optionally be substituted, for example by halogen, alkyl, aryl, cyano, nitro, carbamoyl, carbalkoxy or optionally substituted mercapto.

Suitable radicals B are those of the aniline, ot-aminonaphthalenes Phenol, indole, pyridone, pyrazolone and aminopyrazole series. Preferred are coupling components of the aniline series.

809812/0035 - 2 -

Particularly valuable residues B are those of the formula:

O.Z. 32 186

R-

R-

/ ¹ V /

-R ^J

R ^J

R-

R-

R ^J

whereby

1 2
R, R for hydrogen, optionally substituted alkyl,

Aralkyl or aryl,

R, R for hydrogen, alkyl, aralkyl, halogen, alkoxy, acylamino, Alkylsulfonyl, arylsulfonyl, carbamoyl, carbalkoxy or sulfamoyl,

R stands for hydrogen, alkyl or aryl and X for cyano, carbamoyl, nitro or carbalkoxy »

The carbamoyl and sulfamoyl radicals R ^ and R, and also the Carbamoyl and sulfamoyl radicals representing substituents of A, and the carbamoyl radicals as substituents on the alkyl radicals R and

ρ
R are optionally mono- or dx-substituted by alkyl, aralkyl, aryl, cycloalkyl or the radical of a heterocycle, the

809812/0035

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Substituents including the nitrogen of the carbamoyl or sulfamoyl radical and optionally a further heterocycle can be ring-closed. Residues of such heterocycles are, for example:

O-

or 0 N-

Alkyl groups in the alkylsulfonyl, alkylsulfonylamino, substituted carbamoyl and sulfamoyl radicals and carboxylic acid esters and as substituents of A and as radicals R and R are, for example, those with 1 to 4 carbon atoms, which are optionally replaced by halogen, cyano, hydroxy, oxycarbonyl or C. ₁ - to C ^ -alkoxy can be substituted, specifically for example methyl, ethyl, n- or i-propyl, n- or i-butyl, ß-hydroxyethyl, ß-cyanoethyl, ß-ethoxycarbonylethyl, ß-chloroethyl, ß- Oxycarbonylethyl, ß-hydroxybutyl, ß-methoxyethyl, ß-propoxyethyl, ß-butoxyethyl *

Λ p Γ

Suitable alkyl groups R, R, R and R ^ are z _o B _a those with 1-k carbon atoms, which are optionally substituted by halogen, cyano, hydroxy, C ₁ - to C ^ -alkoxy, benzyloxy, phenoxy, C ₁ to C ^ - Alkylcarbonyloxy, which can optionally be substituted again by an oxycarbonyl radical, oxycarbonyl, C ₁ - to C ^ -alkoxycarbonyl, C ₁ - to C ^ -alkoxycarbonyloxy, carbamoyl, oxalyl, phthalyl, phenylaminocarbonyloxy, C ₁ - to C ^ -alkylaminocarbonyloxy, phenoxycarbonyloxy , Phenylcarbonyloxy or the remainder of a heterocycle such as

• "O '"O' Ό '' O ^or -N ^ W * \ R

R ¹

can be substituted »Examples of such radicals are: methyl, ethyl, propyl, butyl, methoxymethyl, ß-ethoxyethyl, ß-hydroxyethyl, ß-cyanoethyl, ß-chloroethyl, ß-phenoxyethyl, ß-benzyloxyethyl, ß-acetoxyethyl, ß-propionyloxyethyl, ß-Äthoxycarbonyloxyäthyl, ß-Phenoxycarbonyloxyäthyl,

8 09812/0035 -4-

- Ik- * O ₀ line 32 186

ß-ethoxycarbonyl-ethyl, ß-butoxycarbonyl-ethyl, ß-aminocarbonylethyl, ß- (diethylaminocarbonyl) -ethyl, ß- (methylamino-carbonyloxy) -ethyl, ß-C-phenylaminocarbonyloxy-ethyl, ß-oxycarbonyl-ethyl, ß-Oxalyläthyl, ß-Phthaläthyl or the remainder

Λν / ^ n ^ λ

-ch ₂ -ch ₂ -ni, -ch ₂ -ch ₂ -n | , -ch ₂ -ch ₂ -n 0, -ch ₂ -ch ₂ -ch ₂

-CH_-CH "-0-C-0-CH" -CH "-0 or -CH _o -CH" -0-C-CH _o -CH "-C 2 2" 2 2 ν 2 2 "2 2 \

0 OH 0 OH

1 ? R.
Suitable aryl radicals R, R, R, r in the substituted carbamoyl and sulfamoyl groups, the azoaryl radicals, the arylsulfonyl groups and as substituents of A are in particular optionally substituted by phenyl, C ^ - to Cn-alkyl, nitro, halogen, C.- to Cj , -Alkoxy further substituted phenyl or naphthyl radicals, for example phenyl, 1- or 2-naphthyl, p-biphenyl, ^ -chlorophenyl, 2,4-dichlorophenyl, 4-ethoxyphenyl, o-, m- or p-tolyl, 4-nitrophenyl or 4-ethylphenylo

Suitable aralkyl groups as substituents in the sulfamoyl,

1 2 carbamoyl or aralkylsulfonyl groups or as radicals R, R, R, R and R are in particular benzyl or 2-phenylethyl groups _o The phenyl radical of these groups can optionally be replaced by C- to C ₂ , -alkyl, C.- to C ₁ , -Alkoxy, halogen or cyano be further substituted, The following aralkyl groups may be mentioned as examples; Benzyl, 2-phenylethyl, p-methylbenzyl, p-methoxybenzyl, 2,4-dichlorobenzyl, 4-cyanobenzyl, p-bromophenylethyl »

Suitable halogen atoms are fluorine, chlorine, bromine, especially chlorine and bromine »

Suitable alkoxy radicals R, R, R or R ^ and as substituents of A are in particular C ..- to C ₁ , -alkoxy groups, which can optionally be substituted by OH, halogen or cyano, for example methoxy, ethoxy, butoxy, β-hydroxyethoxy , ß-cyanoethoxy or ß-chloroethoxy.

809812/0035. ₅ .

- 9 - ** OoZo 32 186

Suitable acyl groups of the acylamino groups R, R ^ and R are, in particular C ₁ - to C ^ alkanoyl, arylcarbonyl, C ₁ - to C ^ alkylsulfonyl or Arylsulfonylo A suitable aryl group is, in particular the phenyl radical, optionally substituted by C ₁ - to C ^ -Alkyl, C ₁ - to Ch-alkoxy, chlorine or cyano can be substituted = The alkyl groups of the alkylcarbonyl radicals can optionally be substituted by Cl, Cn or by an oxycarbonyl radical »

Examples of acyl radicals include: acetyl, propionyl, methylsulfonyl, ethylsulfonyl, p-methylphenylsulfonyl, phenylsulfonyl, 2,5-dimethylphenylsulfonyl, 2-methyl-5-chlorophenylsulfonyl, p-ethoxybenzoyl, p-chlorobenzoyl, o-chlorobenzoyl, p-cyanobenzoyl or the leftovers

O
-C-CH ₀ -CH ₀ -C ^, -C-CH ₀ -Cl or -C-CH ₀ -CsM ₀

If * - ^ - \ It C. | _t d.

O OH O 0

Dyes of the formula I are obtained by coupling a diazotized amine of the formula

A-NH ₂

with a 2-aminothiazole of the formula II

R.
■ N

NH ₂ II,

<3> iazotize the resulting dye of the formula II

AN = N- ^> NH ₂ III

and coupling to a coupling component B-H, where A, B and R have the meanings given.

The diazotization of the dyes of the formula III and the coupling with B-H are preferably carried out in an anhydrous solvent,

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ZoB. Carboxylic acids, carboxylic acid esters, carboxylic acid amides, hydrocarbons, halogenated hydrocarbons or ethers with esters or salts of nitrous acid as diazotizing agents in the presence of carboxylic acids,

In particular, dimethylformamide, glacial acetic acid and formic acid have proven themselves proven as a solvent and neopentylglycol dinitrite and sodium nitrite as a diazotizing agent »

Suitable amines A-NHp are for example: aniline, 4-toluidine, 4-chloroaniline, 2-nitroaniline, 3-nitroaniline, 4-nitroaniline, 4-cyananiline, 2-chloro-4-nitroaniline, 2-methyl-4-nitroaniline, 2-methoxy-4-nitroaniline, 2-cyano-4-nitroaniline, 2-bromo-4-nitroaniline, 2-trifluoromethyl-4-nitroaniline, 2-nitro-4-methylaniline, 2-nitro-4-chloroaniline, 2, 4-dinitroaniline, 2-nitro-4-methoxyaniline, 2-nitro- ⁱ l-methylsulfonylaniline, 2,4-dicyananiline, 4-acetylaminoaniline, 4-methoxycarbonylaniline, ^ -ethyloxycarbonylaniline, 4-benzyloxycarbonylaniline, ^ -chloro-phenylamine -5- (ß-hydroxyethyl) -aminosulfonylaniline, 2-chloro- ⁱ t-methylsulfonylaniline, 2-methyl-5-nitroaniline, 2-methyl-5-chloroaniline, 3-chloro-4-cyananiline, 2-methoxy-5- chloroaniline, 2, ¹ -dichloroaniline, 2,5-dichloroaniline, 2-cyano-5-chloroaniline, 2-methoxy-4-nitroaniline, 2-cyano-4-nitroaniline, 2,6-dichloroaniline, 2,4,5 -Trichloraniline, 2-chloro-4,6-dinitroaniline, 2-chloro-4-nitro-6-cyananiline, 2,6-dichloro-4-nitroaniline, 2,6-dichloro-4- (dimethyl-aminos sulfonyl) aniline, 2,5-dichloro} - (diethylaminosulfonyl) aniline, 4- (diethylaminosulfonyl) aniline, 2-phenylsulfonylaniline, 4-propylsulfonylaniline, 2 _s 5-dichloro-4-methylsulfonylaniline, 4-aminoazobenzene , 4-methoxy-4'-aminoazobenzene ₉ 1-aminonaphthiazole, 2-aminonaphthalene _s 2-chloro-1-aminonaphthalene _s 6-methyl-2-aminoben2thiazole _s 6-methoxy-2-aminobenzothiazole, 2-amino-4-phenylthiazole _f 2-aminothiazole, 2-airano-5-gyan-2-amino-l ₉ 3 _s 4-thiadiazole, 2-aminoimidaaol, 2-amino-4,5-midazolj, 3 ° ABiino-l ₃ 2 _i) ⁱ i- triasin _s 3-aminobensisothiazole ₉ 6-nitro-3-aminobensisoi; hiazole or 3 ~ aminoindazoI ₀

Suitable 2-Aininothi £ soIa der Forssl II ₉ 2

l, 2 »amino

f? Q fk ί

* Y 3 ¹ Y S

O ₀ Z ₀ 32 186

Suitable coupling components BH are Ν, Ν-dimethylaniline, N, N-diethy! Aniline, N, N-bis- (ß-hydroxyethyl) -aniline, N, N-bis- (ß-chloroethyl) -aniline, N, N- Bis- (ß-cyanoethyl) -aniline, N, N-bis- (ß-acetoxy-ethyl) -aniline, N, N-bis- (ß-ethoxycarbonylethyl) -aniline, N-ethyl-N- (ß-cyanoethyl ) -aniline _s N-methyl-N-benzylaniline, N-benzyl-N- (ß-cyanoethyl) -aniline, N-ethyl-N- (ß-acetoxyethyl) -aniline, N- (ß-acetoxyethyl) -N- (ß-cyanoethyl) -aniline, N-ethyl-N- (ß-chloroethyl) -aniline, N- (ß-cyanoethyl) -N- (ß-benzoyloxyethyl) -aniline, N, N-diethy1-3-methyl- aniline, N-ethyl-N- (ß-cyanoethyl) -3-methyl-aniline, N, N-bis- (ß-acetoxyethyl) -3-methyl-aniline, N, N-bis- (ß-methoxycarbonyloxyethyl) - 3-ethyl-aniline, N- (ß-ethoxyethyl) -N- (ß-cyanoethyl) -3-methyl-aniline, N, N-bis- (ß-cyanoethyl) -3-methyl-aniline, N, N- diethyl-3-chloro-aniline ^t _i N, N-bis- (beta-cyanoethyl) -3-chloro-aniline, N, N-Diäthy1-3-methoxy-aniline, N, N-Diäthy1-3-acetylamino-aniline , N, N-bis (ß-acetoxyethyl) -3-acetylamino-aniline _J N, N-diethyl-3- (ß-cyanoacetylamino) -aniline, N, N-diethyl-3- (methylsulfo nylamino) aniline, N _s N-diethyl-3- (phenylsulfonyl-amino) -aniline, N, N-diethyl-2-methoxy-5-acetylamino-aniline _f N, N-diethyl-2,5-dimethoxy-aniline , N-ethyl-N- (ß-cyanoethyl) -3- (methylsulfonylamino) -aniline, N-ethyl-N- (ß-diethylaminocarbonylethyl) -aniline, N, N-bis- (ß-methylaminocarbonyloxyethyl) -aniline , N-ethyl-N- (ß-phenylaminocarbonyloxyethyl) aniline, 2,6-dihydroxy-3-cyano-4-methyl-pyridine, N-methyl-3-cyano-4-methyl-6-hydroxypyridone-2 , N-ethyl-3-aminocarbonyl-4-methyl-S-hydroxypyridone-2, N-butyl-3-ethoxycarbonyl-4-methyl-6-hydroxypyridone-2, 2-methyl-indole, 1,2 -Dimethylindole _s 2-phenylindole, 1-ß-cyanoethy1-2-pheny1-indole, 1- (2-hydroxy-2-pheny1-ethyl) -2-pheny1-indole, 1- (2-hydroxy-2-methyl- propyl) -2-phenylindole, 2-ethylindole, N, N-diethy1-1-aminonaphthalene, N, N-diethy1-2-aminonaphthalene, N-ethyl-N-benzyl-1-aminonaphthalene, N-benzyl-1-aminonaphthalene , N-ethyl-N- (ß-cyanoethyl) -l-aminonaphthalene, N, N-bis- (ß-ethoxycarbonyloxyethyl) -l-aminonaphthalene, l-phenyl-3-methylpyrazolone -! - 5, 1- (2- Chloropheny 1 ) -jS-methyl-pyrazolone-rS, 1- (2,5-dichlorophenyl) -3-ethyl-pyrazolone-5, l- (4-methylphenyl) -3-carbäthoxypyrazolon-5, l-methyl-3-phenyl- pyrazolon-5, l-ß-cyanoethyl-3- (4-nitropheny1) -pyrazolon ^ 5, l-phenyl-3-methy1-5-amino-pyrazole, l- (4-chlorophenyl) -3-ethyl-5- amino-pyrazole, l-methyl-3-carbethoxy-5-aminopyrazole, 1-ß-chloroethy1-3-pheny1-5-amino-pyrazole, phenol, o- and p-cresol, p-terto-butylphenol, o- and p-chlorophenol »

809812/0035

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The dyes of the invention are suitable for dyeing synthetic fiber materials such as polyamides and polyesters, Z ₀ B ₀ polyethylene terephthalate and poly-1,4-cyclohexane dimethylene terephthalate, from aqueous liquors or organic LösungsmitteIn ₀ Striking is the large coverage of the new dyes "The aforementioned types of fibers are in dyed violet to blue-green shades »The dyeings are characterized by excellent heat-setting fastness properties, good wash fastness properties and good to very good light fastness properties.

Dyes of the formula Ia are of particular industrial importance

R ⁸

AT-. _s ^

in the

A is an optionally substituted phenyl radical,

1 2
R and R optionally substituted alkyl radicals,

R- ^{5 is} hydrogen, C ₁ - to C ^ -alkyl or C ₁ - to C ₄ -AlkOXy, R is hydrogen, chlorine, _s bromine, methyl, ethyl, C ₁ - to C ^ -alkanoylamino or optionally substituted sulfamoyl and

R is hydrogen, optionally substituted alkyl or aryl "

The phenyl radicals A can, for example, by chlorine, bromine, fluorine, trifluoromethyl _s methyl, ethyl, methoxy, ethoxy, arylazo, C ₁ - to Cjj-alkoxycarbonyl, C ₁ - to C ^ -alkoxyethoxycarbonyl, cyano, methylsulfonyl, ethylsulfonyl, C. ₁ - to C N-alkanoylamino or gege gene or substituted carbamoyl or sulfamoyl may be substituted ", Single substituents in addition to the above-mentioned Z ₀ BoS H ₅ C ₆ -N = N-, Cl H ₄ C ₆ -N = N-, H ₃ CH ₄ C ₆ -N = N-, H ₃ COH ₄ C ₆ -N = N-, COOCH ₃ , COOC ₂ H ₅ , COOC ₃ H ₇ , COOC ₄ Hg, COOC ₂ H ₄ OCH ₃ , COOC ₂ H ₄ OC ₂ H ₅ , COOC ₂ H ₄ OC ₄ H ₉ , CO (OC ₂ H ₄ ) ₂ OCH ₃ , CO (OC ₂ H ₄ ) ₂ OC ₄ H _g , CH ₃ CONH,

, H ₇ C ₇ -CONH, CONH (CH _p ), OCH ,, CONHC ₂₁ H ₀ ,

8098Τ270 (Τ35 ^y

- KK 0 "Zo? 2 186

/ ^C 2 ^H 5
CONHCH ₂ CHC, CONHCgH ₁₃ , CONHCgH ₁₇ , CONH (CH J ₂ OC ₂ H ₄ OCg

CONH (CHg) ₃ OC ₂ H ₁₁ OCH ₂ CgH ₅ , CONH (CH ₂ ) 0 (CH ₂ ) ^ OH, COMH (CH ₂ ) OCgH ₁₁ and the corresponding sulfamic residues "

1 2
R and R radicals are, for example, C ₁ - to C ^ -alkyl, which can also be substituted by chlorine, hydroxy, cyano, C ₁ - to C ^ -alkanoyloxy, C ₁ - to Ch-alkoxycarbonyl or phenyl »

Individual radicals are, for example, CH _{1 , C 3} H ₅ , 0, H ₇₉ C 1 -Hq, C ₂ H ₄ Cl C ₂ H ₄ CN, C ₂ H ₄ OH, C ₂ H ₄ OCOCH ₃ , C ₂ H ₄ OCOC ₂ H ₅ , C ₂ H ₄ OCOC ₃ H ₇ , C ₂ H ₄ COOCH ₃ C ₂ H ₄ COOC ₂ H ₅ , C ₂ H ₄ COOC ₃ H ₇ , C ₂ H ₄ COOC ₄ H ₉ , C ₂ H ₄ CH (COOCH ₃ ) ₂ ,

CH ₂ CHOHCH ₃ , CH ₂ CHOHCH ₂ OH, CH ₂ CHOHCH ₂ Cl, CH ₂ CH-CH ₃ , CH ₂ CHCHOCOCH ₃

OCOCH ₃ ( ⁸

CH ₂ CgH ₅ , C ₂ H ₄ CgH ₅ , CH ₂ CH ₂ COCH ₃ or (CH ₂ J ₃ NHCOCH ₃ ,

For R ^ are in addition to hydrogen, for example, CpH ₁ - _s CH ,,, C _{q 4} H, OC ₃ H _7, OC ₄ H _9, and preferably CH _3, OCH ₃ or C ₂ H ₁ - to name _o

Jl

Residues R are, for example, in addition to the % already mentioned NHCHO, NHCOC-H ₇ , SO ₂ NHCH ₃ , SO ₂ NHC ₂ H ₅ , SO ₂ NHC ₃ H ₇ , SO ₂ NHC ₄ H ₉ or SO ₂ NH (CH ₂ ) ^ CH ₃ and preferably NHCOCH, "

8th
Substituents R are besides hydrogen ZOB "optionally substituted by hydroxyl, chlorine, cyano or methyl- mercapto-substituted C ^ - to C ₄ ~ alkyl or optionally substituted by chlorine ₉ bromine, methyl, ethyl, methoxy, ethoxy or cyano-substituted phenyl, in detail thus for example CH ₃₅ C ₃ H ₅₉ C ₃ H ₇₃ C ₄ H _9a CH ₂ OH ₂ CH ₂ Cl ₈ CH ₂ CN, Qi ^^ SCl ^ j, CgH ₄ Cl ₃ CgHjCl ₂ J, CgH ₄ CH ₃₃ CgH ₃ (CH ₃ ) ,,,, CgH ₄ OCH ₃ ;, C ₆ H ₃ (CH ₃ ) OCH ₃ or CgH ₁₁ CNo

In d © n following examples are given over · Parts and percentages © j, unless stated otherwise _s weight ,,

26A0542

OcZ .. 32 186

example 1

47 parts of aniline are dissolved in 150 parts by volume of water and 150 parts of concentrated hydrochloric acid and a solution of 35 parts of sodium nitrite in 50 parts of water is added at 0-5 ° C. After 1 hour, everything is poured into a mixture of 500 parts of ice, 75 parts 2-amino-4-methylthiazole and 500 parts of water. After the addition of sodium acetate and the end of the coupling reaction, the orange-red dye of the formula (a) is filtered off with suction and ^{dried at 50 °} C. »

(a)

6.8 parts of it and 5.2 parts of ß-cyanoethyl-ethyl-aniline are in 150 parts by volume of glacial acetic acid are suspended and 3.1 parts of neopentyl glycol dinitrite are added at 20 ° C. After stirring for four hours, at The mixture is poured onto ice at room temperature and the blue-violet dye of the formula (b) is filtered off with suction. Yield: 11.2 parts,

C ₂ H ₅

(b)

Example 2

6.3 parts of the dyestuff of the formula (a) are dissolved together with 5.2 parts of β-cyanoethylethylaniline in 100 parts of formic acid and 2 parts of _β sodium nitrite are added in portions at 10 ° C. After 4 hours, the mixture is poured onto ice and the separated product is sucked off Dye of the formula (b) from »
Yield: 5 »1 parts«

Example 3

81 parts of 2,4-dichloroaniline are dissolved in 4Ό & parts of half-concentrated hydrochloric acid in the heat, then the mixture is ^{cooled to 0} ° C. and diazotized with 35 parts of sodium nitrite dissolved in a little water.

The diazonium salt solution is coupled as described in Example 1 with 2-amino-4-methyl-thiazole "The orange azo dye of the formula (c) is obtained

(c)

8.6 parts of this dye, 5.2 parts and ß-chloro-ethylaniline 1 part of trichloroacetic acid is dissolved in 100 parts by volume of dimethylformamide and mixed with 2.8 parts of neopentyl glycol dinitrite at room temperature offset. After stirring for three hours at room temperature, the mixture is poured onto 400 parts of ice and the blue-green dye of the formula (d) sucked off. Yield: 10.2 parts

Cl H, C

(d) C ₂ H ₄ Cl

Example 4

5.9 parts of the dye of the formula (c) are dissolved in 90 parts of phosphoric acid (85 %) , 50 parts of glacial acetic acid and 30 parts of propionic acid, and 9 parts of nitrosulfuric acid (12.8 % NpO,) are added at 0-5 ° C. added dropwise. "After 3 hours, the mixture is poured into 3.4 parts of β-cyanoethyl-ethylaniline and 300 parts of ice." After blunting with 60 parts of sodium format and the coupling is complete, the blue dye is filtered off with suction. "Yield; 1.8 parts of the dye of the formula (d) _o

The dyes listed in the table were prepared analogously to the procedure described in Examples 1-4.

- 12 -

809812/0035

O ₀ line 32 186

Tabel

For example, Diazo 1 »coupling backlash component component 2 "Coupling component color

in DMP

NH, f ~ \

• Ν.

violet

6 Br

• NIL blue-violet

7 cl

NH.

8 cl

NH,

Cl

9 O ₉ N

blue

blue green

ίο c ₂ h ₅ ooc - / _ \ nk ₂ "blue

F \

• N

, C ₂ H ₄ COOCH

V = / C ₂ H ₅

Cl

13 i ¹ Vnh, CH,

C ₂ H ₄ COOCH ₃

809812/0035

0.Z ₀ 32 186

In- Diazo- 1st clutch play component component

2. Coupling component color

in DMP

Cl

14 ei- / Vnh,

/ ^C 2 ^H 5

blue

CH.

NH-

.C ₀ Hj ₁ COOCH, ^{2 4}

-N

violet

NH ₂ "

C ₀ H ₁₁ CN / 24

^C 2 ^H 5

blue-violet

/ Λ

-NH.

C ₂ H ₁₁ COOCH

CH,

Cl H ₃ C

18 Cl- (Z \> NH ₂ //

blue

Cl

CP

, C ₂ H ₁₁ COOCH ₃

C ₂ H ₅

, C ₂ H ₄ CN

C ₂ H ₅

NH,

NHCQCH,

blue green

-Λ <β

O ₀ Z ₀ 32 186

With- Diazo- 1 “coupling- 2nd coupling component color tone game component component in DMF

H, C

H ₃ CO

NHCOCH-

blue green

2k ff

CN

Cl

NH,

CF,

, C ₂ H ₄ COOCH ₃

C ₂ H ₅

blue

NH,

C ₂ H ₅ blue
violet C ₂ H ₄ COOCH ₃ blue C ₂ H ₅

CH

NH,

- N i

blue green

Cl

809812/0035

- 15 -

- 15 -

oZo 32 186

For example, Diazo- Io coupling backlash component component 2 "Coupling component color

in DMF

H, C

/ ^NH 2

O-

NH,

(CH ₂ )

blue

NH

C ₂ H ₂₁ COOCH ₃

green Blue

809812/0035

NM. INSPECTS

Claims (1)

- * 6 - OoZο 32 186 Patent claims _Λ _ Ι »Azo dyes of the general formula R.
VN A-N = N- ^ g> N = N-B in the A is the remainder of a diazo component, B the remainder of a coupling component and R is hydrogen, halogen, an optionally substituted hydrocarbon radical, optionally substituted alkoxy or aroxy or substituted amino, 2 "Azo dyes according to claim 1 of the formula R ⁸ r3 VN
A ¹ -N = N- ^ ₃ in the A is an optionally substituted phenyl radical _s 1 2
R and R optionally substituted alkyl radicals, R · ^{5 is} hydrogen, C ₁ - to C ^ -alkyl or C ₁ - to C ^ -alkoxy, R is hydrogen, chlorine, bromine, methyl, ethyl, C ₁ - to C ^ -alkanoylamino or optionally substituted sulfamoyl and R is hydrogen, optionally substituted alkyl or aryl, 3. Process for the preparation of azo dyes according to Claim 1, characterized in that a diazo compound of amines of the formula AN = N- ^> -NH _?
'S 809812/0035 ~ ¹⁷ ~ ORiQlNAL INSPECTED - *? -H OoZ. 32 186 with a coupling component of the formula HB
implements, 4. The use of the azo dyes according to claim 1 for dyeing synthetic textile material. BASF Aktiengesellschaft cent 809812/0035